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When the Chicago Teachers Union (CTU) first went on strike in 1969, many Black teachers crossed the picket line. They argued that any benefits that might come from the strike would never reach Black educators, Black students, or Black communities. They had good reason to be skeptical of the union. For years Black teachers had been systemically relegated to full-time basis substitute status and marginalized by the union, which was largely under the control of the city’s powerful Democratic political machine. At the time, some Black teachers were fighting for inclusion in the union, while others, inspired by the Black Power movement, were working to create alternative institutions and organizations of Black educators grounded in Black self-determination. Karen Lewis’s parents navigated this historical moment as Black teachers. At the same time, Karen--who would later go on to lead the CTU--was organizing Black student walkouts for community control as a high school student. I was also a teacher during this time. In this commentary, I will draw on my scholarly expertise in urban education, cultural contexts of learning, and teacher preparation, as well as my nearly 60 years of experience as an educator and school founder, to discuss the importance of the Black Power era in the development of Black educators and Black education within and beyond the public schools.